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Sulfonium sulfonate photoacid generator synthesized from abietic acid and synthesis method of sulfonium sulfonate photoacid generator

A technology of photoacid generator and synthesis method, which is applied in the field of photoresist, can solve the problems of exposure influence, poor transparency, etc., and achieve the effects of excellent etching resistance, uniform dissolution, and simple synthesis route

Inactive Publication Date: 2021-04-13
上海博栋化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional sulfonium salt has poor transparency at 193nm because of its benzene ring structure, which has an impact on subsequent exposure

Method used

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  • Sulfonium sulfonate photoacid generator synthesized from abietic acid and synthesis method of sulfonium sulfonate photoacid generator
  • Sulfonium sulfonate photoacid generator synthesized from abietic acid and synthesis method of sulfonium sulfonate photoacid generator
  • Sulfonium sulfonate photoacid generator synthesized from abietic acid and synthesis method of sulfonium sulfonate photoacid generator

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Experimental program
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Effect test

Embodiment 1

[0038]

[0039] The first step: Abietic acid 1-1 (10g, 33.1mmol), 1,1-difluoro-2-hydroxyl ethane-1-sodium sulfonate (6.1g, 33.1mmol) was added in toluene (100g), Add p-toluenesulfonic acid (0.8g, 4.6mmol), the reaction solution was heated to reflux for 16 hours, the reaction solution was cooled and filtered to obtain a solid, the solid was washed three times with acetonitrile (100g×3), the mixed acetonitrile solution was concentrated, and added to Beat in methyl tert-butyl ether (100 g), filter the above mixed solution, collect and dry the filter cake to obtain solid compound 1-2 (12.5 g, 26.7 mmol, yield 80.6%);

[0040] The second step: under the protection of nitrogen flow, (cyclohexa-1,5-dienyloxy)-trimethyl-silane (4.5g, 26.7mmol) and tetramethylene sulfoxide (2.8g, 26.9 mmol) solution in chloroform (250g), cooled to -30 degrees Celsius, slowly added trifluoroacetic anhydride (8g, 38.1mmol) within 30 minutes, stirred for 30 minutes, added 1-2 (12.5g, 26.7mmol) of satu...

Embodiment 2

[0042]

[0043] The first step: abietic acid 2-1 (10g, 33.1mmol), 1,1,2,2-tetrafluoro-3-hydroxypropane-1-sodium sulfonate (7.7g, 32.9mmol) and sulfuric acid (0.5g , 5.1 mmol) was added to toluene (150 g), heated to reflux for 18 hours and cooled to room temperature. The mixture was filtered to obtain a solid, which was washed three times with acetonitrile (100 g x 3). Concentrate the mixed acetonitrile solution, and add it into methyl tert-butyl ether (100g) for beating, filter the above mixed solution, collect and dry the filter cake to obtain intermediate 2-2 (13.5g, 26.0mmol, yield 78.7%).

[0044] The second step: under the protection of nitrogen flow, (cyclohexa-1,5-dienyloxy)-trimethyl-silane (4.4g, 26.1mmol) and tetramethylene sulfoxide (2.7g, 25.9 mmol) was dissolved in chloroform (200g), cooled to -30 degrees Celsius, slowly added trifluoroacetic anhydride (6.5g, 30.9mmol) within 30 minutes, stirred for 30 minutes, and added 2-2 (13.5g , 26.0mmol) of saturated a...

Embodiment 3

[0046]

[0047]The first step: abietic acid (10g, 33.1mmol) is dissolved in anhydrous tetrahydrofuran (100g), cooled to 0 degrees Celsius with an ice-water bath, under the protection of a nitrogen stream, slowly add lithium aluminum hydride (2.5g, 65.9mmol), The reaction solution was heated to reflux for 12 hours, the reaction solution was cooled to 0 degrees Celsius, 2.5 g of water was added, and 15% sodium hydroxide solution (6 g) was slowly added dropwise, then 7.5 g of water was added, raised to room temperature and stirred for half an hour, and 50 g of tetrahydrofuran was added to dilute , filtered with a funnel equipped with diatomaceous earth, the filter cake was washed with tetrahydrofuran (50g), the filtrate was dried over anhydrous sodium sulfate, and concentrated under vacuum to obtain intermediate 3-2 (9.1g, 31.5mmol, yield: 95.4% ).

[0048] The second step: join intermediate 3-2 (9.1g, 31.5mmol), sodium carboxydifluoromethanesulfonate (6.2g, 31.3mmol) in tolue...

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Abstract

The invention discloses a sulfonium sulfonate photoacid generator synthesized from abietic acid, and relates to the field of photoacid generators. The sulfonium sulfonate photoacid generator has a structural formula shown in the specification, in the formula, R1 is an oxygen-containing linking group, and R2 is a fluoroalkyl group. The photoacid generator can reduce the diffusion of the photoacid generator, improve the edge roughness, reduce the line width roughness and improve the resolution; the photoacid generator is more transparent under 193 nm, and exposure under a 193 nm light source is facilitated; the etching resistance is excellent; the photoacid generator is balanced in hydrophilicity and lipophilicity, has proper adhesive force and excellent solubility, is more uniform in dissolution, and is simple in synthetic route.

Description

technical field [0001] The invention relates to the field of photoresists, in particular to a sulfonate sulfonium salt photoacid generator synthesized from abietic acid and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the process of transferring the pattern designed on the mask plate to the substrate by using the chemical sensitivity of photoresist under the action of visible light, ultraviolet light, electron beam, etc., through exposure, development, etching and other processes. Graphics microfabrication technology. [0003] Photoresist, also known as photoresist, is the most critical functional chemical material involved in photolithography technology. The main components are resin, photoacid generator, and corresponding additives and solvents. This type of material has light (including Visible light, ultraviolet light, electron beam, etc.) are chemically sensitive, and their solubility in the developer solution changes ...

Claims

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Application Information

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IPC IPC(8): C07C309/12C07C309/17C07C303/32C07D333/46G03F7/004
CPCC07C309/12C07C309/17C07C303/32C07C29/147C07D333/46G03F7/0045C07C2603/26C07B2200/07C07C33/14
Inventor 潘惠英蒋小惠李嫚嫚贺宝元毕景峰
Owner 上海博栋化学科技有限公司
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